Add vanilla pudding mix and water to a large bowl. Whisk until combined, add the sweetened condensed milk and whisk again.
Cover the bowel and transfer to the fridge for at least 4 hours, or overnight until fully set.
Once pudding if fully set, make your whipped cream. Blend dried strawberries (food processor, blender, or smash using a large zip lock bag) to make powdered strawberries.
Using a stand mixer or hand mixer whisk 3 cups of heavy cream until soft peaks form. Gently fold in dried strawberry powder until combined.
In a separate bowl, combine sliced strawberries with 1 tbsp sugar and allow to sit for 10 minutes until the juices pull at the bottom of the bowl.
Add 1/3 of the whipped cream mixture into the pudding mixture. Gently stir until the whipped cream is fully incorporated. Fold in the remaining whipped cream and gently mix until smooth.
Assembly time! Layer a few spoonfuls of the pudding mixture into a large bowl. Add a few scoops of strawberries (don’t leave behind those juices!), then add more pudding, followed by the graham crackers. Pudding. Strawberries. Pudding. Graham crackers. Repeat!
Cover the bowl and allow to set in the fridge for at least 1 hour up to overnight. Scoop into bowls and enjoy!